Dimethylformamide → 2-Amino-6-(3-(2-amino-phenyl)allyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

HRID 974329Notes

Reaction equation

HRID 974329 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:12][CH:13]=[CH:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+]([O-])=O)[CH:16]=3)[CH2:8][CH2:9][C:10]=2[N:11]=1.C[N:25](C)C=O>[Ni]>[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:12][CH:13]=[CH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[NH2:25])[CH2:8][CH2:9][C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 541074592-Amino-6-(3-(3-nitro-phenyl)allyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

Product 1

HCID 542601432-Amino-6-(3-(2-amino-phenyl)allyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Prepared by catalytic hydrogenation of 2-amino-6-(3-(3-nitro-phenyl)allyl)-4,5,7,8-tetrahydro-6H- thiazolo[5,4-d]azepine using Raney nickel in anhydrous dimethylformamide (4.5 hours at ambient temperature). After purification by column chromatography the base is dissolved in isopropanol. By the addition of ethereal hydrochloric acid, cooling, filtering and drying at 100° C./0.1 torr over phosphorus pentoxide the title compound is obtained. Yield: 37% of theory, Melting point: 160° C. (decomp.).

Workup

  1. customAfter purification by column chromatography the base
  2. dissolutionis dissolved in isopropanol
  3. additionBy the addition of ethereal hydrochloric acid
  4. temperaturecooling
  5. filtrationfiltering
  6. dry with materialdrying at 100° C./0.1 torr over phosphorus pentoxide the title compound
  7. customis obtained

Sources & evidence

ORD record
ord-2dd956070f6b4c90a34b41328361392d
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Reaction notes

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